3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-6-one | 768382-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-6-one
• 英文别名: 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta[c]chromen-3-yl)oxy]oxan-2-yl]methyl acetate
• CAS: 768382-32-7
• 化学式: C₂₈H₃₂O₁₂
• 分子量: 560.555
• InChiKey: GZYJQIYKODJQNJ-JBMSBTKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-6-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以83%的产率得到3-(β-D-glucopyranosyloxy)-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-6-one
  参考文献：
  名称：

  Modified Coumarins. 12. Synthesis of 3,4-Cycloannelated Coumarin  -D-Glucopyranosides

  摘要：

  O-beta-D-Glucopyranosides were synthesized using 3,4-cycloannelated hydroxycoumarins as aglycons. Phenolic hydroxyls were O-glycosylated via condensation of coumarin potassium salts with acetobromoglucose in homogeneous medium and in a liquid-liquid system using a phase-transfer catalyst.

  DOI：

  10.1023/b:conc.0000025455.68950.36
• 作为产物：
  描述：

  2-氧代-1-环庚烷甲酸甲酯 在 氢氧化钾 、 硫酸 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-6-one
  参考文献：
  名称：

  Modified Coumarins. 12. Synthesis of 3,4-Cycloannelated Coumarin  -D-Glucopyranosides

  摘要：

  O-beta-D-Glucopyranosides were synthesized using 3,4-cycloannelated hydroxycoumarins as aglycons. Phenolic hydroxyls were O-glycosylated via condensation of coumarin potassium salts with acetobromoglucose in homogeneous medium and in a liquid-liquid system using a phase-transfer catalyst.

  DOI：

  10.1023/b:conc.0000025455.68950.36